EP1568700A1 - S-triazine derivatives containing at least two silated p-aminobenzalmalonate groups, sunscreen compositions containing these derivatives as well as the use of the derivatives - Google Patents

Abstract

Silanic para-aminobenzalmalonate substituted S-triazine compounds (I) are new. Silanic para-aminobenzalmalonate substituted S-triazine compounds of formula (I) are new. R 1-R 3optionally saturated 1-10C alkyl (optionally substituted with one or more halo), phenyl or CH 3; p : 0-1; A : H, optionally saturated 1-8C alkyl, phenyl or Si(CH 3) 3, provided that when A is Si(CH 3) 3, then p is 0; W 1optionally saturated 1-8C alkylene (optionally substituted by hydroxyl group); Z : (C=O)OR 4, -(C=O)R 5, -(C=O)NR 6R 7, -SO 2R 8, CN or (C=O)YCHA(W 1) pSiR 1R 2R 3; R 4H or an optionally saturated 1-20C alkyl radical; R 5, R 81-20C alkyl or 6-12C aryl; R 6, R 7H or 1-20C alkyl; Y : O or NR 7; and B 1chromophoric group of para-aminobenzalmalonate, aminobenzimidazole, benzimidazole, aminobenzoate, aminosalicylate, anthranilate, aminobenzylidenecamphor, aminobenzotriazole, aminobenzoxazole or para aminophenylbenzoxazole substituents, provided that B 1can also be 1-20C aminoalkyl or 6-20C aryl radical which can be optionally substituted by alkyl, hydroxyl and/or alkoxy. Independent claims are also included for: (1) a topically applicable UV-photoprotective cosmetic/dermatological composition (A) comprising (I) and a cosmetic/dermatological vehicle; (2) a regime or regimen for the UV-photoprotection of the skin against the damaging effects of UV-radiation and for controlling the variation in the color of the skin due to UV-radiation comprising topically applying (A); and (3) a synthetic polymer or glass comprising a photostabilizing amount of (I). [Image] ACTIVITY : Dermatological. MECHANISM OF ACTION : None given.

Description

The invention relates to novel s-triazine derivatives having at least 2 particular para-amino benzalmalonate groups and their uses in cosmetic.

The invention also relates to photoprotective compositions, comprising s-triazine derivatives having at least 2 para-amino groups benzalmalonate grafted as active solar filters in the field of UV radiation.

It is known that the radiation of wavelengths between 280 nm and 400 nm allow the browning of the human epidermis, and that radiation from wavelengths between 280 and 320 nm known under the name UV-B radiation, cause erythema and skin burns that can interfere with the development of natural tanning.

It is also known that UV-A rays of wavelengths between 320 and 400 nm, causing browning of the skin, are likely to induce an alteration of it, especially in the case of sensitive skin and / or continuously exposed to solar radiation. UV-A rays lead in particular to a loss of elasticity of the skin and the appearance of wrinkles leading to premature cutaneous aging. They favor the trigger the erythematous reaction or amplify this reaction in certain subjects and may even be the cause of phototoxic reactions or photoallergic. Thus, for aesthetic and cosmetic reasons such as preserving the natural elasticity of the skin, more and more people want to control the effect of UV-A on their skin. Factor of sun protection the ratio of the irradiation time necessary to reach the erythematogenic threshold in the presence of the filter tested at the time of irradiation necessary to reach the same threshold in the absence of filter.

It is therefore desirable to have compounds capable of absorbing UV-A rays.

In addition to their ability to filter UV-A radiation, the compounds sought-after photoprotective agents must also have good properties cosmetics, a good solubility in the usual solvents and in particular in fatty substances such as oils and greases, as well as good resistance water and perspiration (remanence) and satisfactory photostability.

Among all the compounds which have been recommended for this purpose, mention may be made of especially s-triazine derivatives bearing benzalmalonate substituents described in the application EP 0 507 691 of the Applicant. These compounds possess, however, a liposolubility and photochemical stability which are not not yet fully satisfactory.

The Applicant has surprisingly discovered a new family of s-triazine derivatives carrying at least 2 para-aminobenzalmalonate groups silanic having good absorbing properties in the range of long UV-A rays and having solubility in body fat, photostability, as well as cosmetic qualities clearly improved compared to s-triazine derivatives grafted with benzalmalonates of the prior art discussed above.

The invention relates to a novel family of s-triazine derivatives having a minus 2 particular para-aminobenzalmalonate groups of formula (I) which will be defined later in detail.

The invention also relates to a cosmetic composition or Dermatological, intended for the photoprotection of keratin materials, containing in a cosmetically acceptable medium at least one compound of formula (I).

Other objects will appear in the light of the description.

dans laquelle :

• les radicaux R₁, R₂ et R₃ identiques ou différents, représentent un radical alkyle en C₁-C₁₀, linéaire ou ramifié, saturé ou insaturé, pouvant comporter un ou plusieurs atomes d'halogène (par exemple CI, Br, F) ; un radical phényle,
• p est égal à 0 ou 1,
• A désigne hydrogène ; un radical alkyle en C₁-C₈, linéaire ou ramifié, saturé ou insaturé; un radical phényle ; le groupe Si(CH₃)₃, sous réserve que lorsque A est Si(CH₃)₃, alors p = 0 et R₁, R₂ et R₃ sont méthyle,
• W est un radical alkylène en C₁-C₈, linéaire ou ramifié, saturé ou insaturé, éventuellement substitué par un radical hydroxyle,
• Z désigne -(C=O)OR₄ , -(C=O)R₅, -(C=O)NR₆R₇ , -SO₂R₈ , -CN ou -(C=O)YCHA(W)_pSiR₁R₂R₃ ,
• le radical R₄ désigne hydrogène ; un radical alkyle en C₁-C₂₀, linéaire ou ramifié, saturé ou insaturé,
• le radical R₅ désigne un radical alkyle en C₁-C₂₀, linéaire ou ramifié, éventuellement cyclique ; un aryle en C₆-C₁₂,
• les radicaux R₆, R₇, identiques ou différents représentent hydrogène ; un alkyle en C₁-C₂₀, linéaire ou ramifié,
• Y désigne -O- ou -NR₇-,
• le radical R₈ désigne un radical alkyle en C₁-C₂₀, linéaire ou ramifié ; un aryle en C₆-C₁₂.
• B₁ désigne un groupe chromophore choisi parmi ceux du type para amino benzalmalonate, amino benzimidazole, benzimidazole, amino benzoate, amino salicylate, anthranilate, amino benzylidène camphre, amino benzotriazole, amino benzoxazole, para aminophényl benzoxazole ;
• B₁ peut également désigner un groupe aminoalkyle en C₁-C₂₀, linéaire ou ramifié ; un groupe aryle en C₆-C₂₀ substitué ou non par des radicaux alkyles, hydroxy et alkoxy.

The compounds according to the present invention have the following general formula (I):

in which :

• the radicals R ₁ , R ₂ and R _{3 which are} identical or different, represent a linear or branched, saturated or unsaturated C ₁ -C ₁₀ alkyl radical which may comprise one or more halogen atoms (for example Cl, Br, F ); a phenyl radical,
• p is 0 or 1,
• A is hydrogen; a linear or branched, saturated or unsaturated C ₁ -C ₈ alkyl radical; a phenyl radical; the group Si (CH ₃ ) ₃ , provided that when A is Si (CH ₃ ) ₃ , then p = 0 and R ₁ , R ₂ and R ₃ are methyl,
• W is a linear or branched, saturated or unsaturated C ₁ -C ₈ alkylene radical, optionally substituted with a hydroxyl radical,
• Z is - (C = O) OR ₄ , - (C = O) R ₅ , - (C = O) NR ₆ R ₇ , -SO ₂ R ₈ , -CN or - (C = O) YCHA (W) _p SiR ₁ R ₂ R ₃ ,
• the radical R ₄ denotes hydrogen; a linear or branched, saturated or unsaturated C ₁ -C ₂₀ alkyl radical,
• the radical R ₅ denotes a linear or branched, optionally cyclic, C ₁ -C ₂₀ alkyl radical; a C ₆ -C ₁₂ aryl,
• the radicals R ₆ , R ₇ , which may be identical or different, represent hydrogen; a linear or branched C ₁ -C ₂₀ alkyl,
• Y denotes -O- or -NR ₇ -,
• the radical R ₈ denotes a linear or branched C ₁ -C ₂₀ alkyl radical; a C ₆ -C ₁₂ aryl.
• B ₁ denotes a chromophoric group chosen from those of the para amino benzalmalonate, amino benzimidazole, benzimidazole, amino benzoate, amino salicylate, anthranilate, amino benzylidene camphor, amino benzotriazole, amino benzoxazole, para aminophenyl benzoxazole type;
• B ₁ may also denote a linear or branched C ₁ -C ₂₀ aminoalkyl group; a C ₆ -C ₂₀ aryl group substituted or unsubstituted with alkyl, hydroxy and alkoxy radicals.

Although in formula (I) above, only the isomers are represented in which the substituent Z is in cis position relative to the substituent at aromatic nucleus, this formula should be understood as also encompassing the corresponding trans isomer.

In formula (I) above, the alkyl radicals can be linear or branched, saturated or unsaturated and chosen especially from methyl radicals, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and ter-octyl. The radical Particularly preferred alkyl is the methyl radical.

In the formula (I) above, the alkoxy radicals are linear or branched, saturated or unsaturated and preferably selected from methoxy, ethoxy, n-propyloxy, n-butyloxy.

In the formula (I) above, the aryl radicals are preferably phenyl.

dans laquelle Z, A, p, W, R₁, R₂ et R₃ ont les mêmes significations indiquées précédemment.According to one particular form of the invention, the compounds of formula (I) may comprise 3 silane para-aminobenzalmalonate groups, namely that B ₁ denotes a group of formula (II) below:

in which Z, A, p, W, R ₁ , R ₂ and R ₃ have the same meanings indicated above.

• Z = -(C=O)OR₅ , -CN ou (C=O)YCHA(W)_pSiR₂R₃R₄,
• R₅ est méthyle ou éthyle,
• A est H,
• R₂ à R₄ désignent alkyle en C₁-C₄ et plus préférentiellement méthyle,
• n est 0,
• p est 0 ou 1,
• W est un radical alkylène en C₁-C₂.

The compounds of formula (I) preferably have at least one, and even more preferably all, of the following characteristics:

• Z = - (C = O) OR ₅ , -CN or (C = O) YCHA (W) _p SiR ₂ R ₃ R ₄ ,
• R ₅ is methyl or ethyl,
• A is H,
• R ₂ to R ₄ denote C ₁ -C ₄ alkyl and more preferably methyl,
• n is 0,
• p is 0 or 1,
• W is a C ₁ -C ₂ alkylene radical.

Among the compounds of formula (I) that are more particularly preferred, mention will be made of those compounds of formulas (1) to (6) below:

dans lequel R₁, R₂, R₃, A, B₁, Y, W, Z et p ont la définition de la formule (I) ci-dessus et X représente un halogène, en particulier le chlore ou le brome.The compounds of formula (I) can be obtained according to the following scheme (a)

wherein R ₁ , R ₂ , R ₃ , A, B ₁ , Y, W, Z and p have the definition of formula (I) above and X represents a halogen, in particular chlorine or bromine.

The reactions above can be carried out optionally in the presence solvent (for example: toluene, xylene or acetone / water) at a between 0 ° C and 250 ° C, more particularly between 5 ° C and 150 ° C.

The compounds of formula (III) can be prepared according to methods described, for example, in EP 0 507 691 Applicant.

dans lequel R₁, R₂, R₃, A, W, Z et p ont la définition de la formule (I) ci-dessus et R₉ est méthyle ou éthyle.In the case where Y is -O-, the compounds of formula (I) may also be obtained by transesterification of derivatives of formula (IV) according to Scheme (b) below:

wherein R ₁ , R ₂ , R ₃ , A, W, Z and p have the definition of formula (I) above and R ₉ is methyl or ethyl.

The compounds of formula (I) are generally present in the composition of the invention in proportions of between 0.01% and 20% by weight, preferably between 0.1% and 10% by weight, relative to the total weight of the composition.

The compositions according to the invention may comprise in addition to other complementary organic or inorganic UV filters active in the AVU and / or water-soluble or fat-soluble or solvent-insoluble UVB commonly used cosmetics.

The complementary organic screening agents are chosen in particular from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; the salicylic derivatives, camphor derivatives; triazine derivatives other than those of the invention such as those described in US patent applications 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469, EP933376, EP507691, EP507692, EP790243, EP944624; the benzophenone derivatives; derivatives of β, β-diphenylacrylate; drifts benzotriazole; benzalmalonate derivatives; derivatives of benzimidazole; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; the derivatives of p-aminobenzoic acid (PABA); methylene bis (hydroxyphenyl) derivatives benzotriazole) as described in US applications 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; ; derivatives of benzoxazole as described in patent applications EP0832642, EP1027883, EP1300137 and DE10962844; the filters and silicones polymers filters such as those described in particular in the application WO-93/04665; the dimers derived from α-alkylstyrene such as those described in the application for DE19855649 patent; 4,4-diarylbutadienes as described in applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EP1133980 and EP133981 and mixtures thereof.

Dérivés de l'acide para-aminobenzoique :

PABA,

Ethyl PABA,

Ethyl Dihydroxypropyl PABA,

Ethylhexyl Diméthyl PABA vendu notamment sous le nom « ESCALOL 507 » par ISP,

Glyceryl PABA,

PEG-25 PABA vendu sous le nom « UVINUL P25 » par BASF,

Dérivés salicyliques :

Homosalate vendu sous le nom « Eusolex HMS » par Rona/EM Industries,

Ethylhexyl Salicylate vendu sous le nom « NEO HELIOPAN OS » par HAARMANN et REIMER,

Dipropyleneglycol Salicylate vendu sous le nom « DIPSAL » par SCHER,

TEA Salicylate, vendu sous le nom « NEO HELIOPAN TS » par HAARMANN et REIMER,

Dérivés du dibenzoylméthane :

Butyl Methoxydibenzoylmethane vendu notamment sous le nom commercial « PARSOL 1789 » par HOFFMANN LA ROCHE,

Isopropyl Dibenzoylmethane,

Dérivés cinnamiques :

Ethylhexyl Methoxycinnamate vendu notamment sous le nom commercial « PARSOL MCX » par HOFFMANN LA ROCHE,

Isopropyl Methoxy cinnamate,

Isoamyl Methoxy cinnamate vendu sous le nom commercial « NEO HELIOPAN E 1000 » par HAARMANN et REIMER,

Cinoxate, DEA Methoxycinnamate, Diisopropyl Methylcinnamate,

Glyceryl Ethylhexanoate Dimethoxycinnamate

Dérivés de β,β'-diphénylacrylate :

Octocrylene vendu notamment sous le nom commercial « UVINUL N539 » par BASF,

Etocrylene, vendu notamment sous le nom commercial « UVINUL N35 » par BASF,

Dérivés de la benzophénone :

Benzophenone-1 vendu sous le nom commercial « UVINUL 400 » par BASF,

Benzophenone-2 vendu sous le nom commercial « UVINUL D50 » par BASF

Benzophenone-3 ou Oxybenzone, vendu sous le nom commercial « UVINUL M40 » par BASF,

Benzophenone-4 vendu sous le nom commercial « UVINUL MS40 » par BASF,

Benzophenone-5

Benzophenone-6 vendu sous le nom commercial « Helisorb 11 » par Norquay

Benzophenone-8 vendu sous le nom commercial « Spectra-Sorb UV-24 » par American Cyanamid

Benzophenone-9 vendu sous le nom commercial« UVINUL DS-49» par BASF,

Benzophenone-12

2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle.

Dérivés du benzylidène camphre :

3-Benzylidene camphor fabriqué sous le nom « MEXORYL SD» par CHIMEX,

4-Methylbenzylidene camphor vendu sous le nom « EUSOLEX 6300 » par MERCK,

Benzylidene Camphor Sulfonic Acid fabriqué sous le nom « MEXORYL SL» par CHIMEX,

Camphor Benzalkonium Methosulfate fabriqué sous le nom « MEXORYL SO » par CHIMEX,

Terephthalylidene Dicamphor Sulfonic Acid fabriqué sous le nom « MEXORYL SX » par CHIMEX,

Polyacrylamidomethyl Benzylidene Camphor fabriqué sous le nom « MEXORYL SW » par CHIMEX,

Dérivés du phenyl benzimidazole :

Phenylbenzimidazole Sulfonic Acid vendu notamment sous le nom commercial « EUSOLEX 232 » par MERCK,

Disodium Phenyl Dibenzimidazole Tetra-sulfonate vendu sous le nom commercial commercial « NEO HELIOPAN AP » par HAARMANN et REIMER,

Dérivés de la triazine :

Anisotriazine vendu sous le nom commercial «TINOSORB S » par CIBA GEIGY,

Ethylhexyl triazone vendu notamment sous le nom commercial «UVINUL T150 » par BASF,

Diethylhexyl Butamido Triazone vendu sous le nom commercial « UVASORB HEB » par SIGMA 3V,

Dérivés du phenyl benzotriazole :

Drometrizole Trisiloxane vendu sous le nom « Silatrizole » par RHODIA CHIMIE Methylène bis-Benzotriazolyl Tetramethylbutylphénol, vendu sous forme solide sous le nom commercial « MIXXIM BB/100 » par FAIRMOUNT CHEMICAL ou sous forme micronisé en dispersion aqueuse sous le nom commercial « TINOSORB M » par CIBA SPECIALTY CHEMICALS,

Dérivés anthraniliques :

Menthyl anthranilate vendu sous le nom commercial commercial « NEO HELIOPAN MA » par HAARMANN et REIMER,

Dérivés d'imidazolines :

Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate,

Dérivés du benzalmalonate :

Polyorganosiloxanes à fonction benzalmalonate tels que le Polysilicone-15 vendu sous la dénomination commerciale « PARSOL SLX » par HOFFMANN LA ROCHE

Dérivés de 4,4-diarylbutadiène :

-1,1-dicarboxy (2,2'-diméthyl-propyl)-4,4-diphénylbutadiène

Dérivés de benzoxazole :

2,4-bis-[5-1(diméthylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imino-1,3,5-triazine vendu sous le nom Uvasorb K2A par Sigma 3V ;

et leurs mélanges. As examples of complementary organic filters, mention may be made of those designated below under their INCI name:

Derivatives of para-aminobenzoic acid:

PABA

Ethyl PABA,

Ethyl Dihydroxypropyl PABA,

Ethylhexyl Dimethyl PABA sold in particular under the name "ESCALOL 507" by ISP,

Glyceryl PABA,

PEG-25 PABA sold under the name "UVINUL P25" by BASF,

Salicylic derivatives:

Homosalate sold under the name "Eusolex HMS" by Rona / EM Industries,

Ethylhexyl Salicylate sold under the name "NEO HELIOPAN OS" by HAARMANN and REIMER,

Dipropylene glycol salicylate sold under the name "DIPSAL" by SCHER,

TEA Salicylate, sold under the name "NEO HELIOPAN TS" by HAARMANN and REIMER,

Derivatives of dibenzoylmethane:

Butyl Methoxydibenzoylmethane sold in particular under the trade name "PARSOL 1789" by HOFFMANN LA ROCHE,

Isopropyl Dibenzoylmethane,

Cinnamic derivatives:

Ethylhexyl methoxycinnamate sold in particular under the trade name "PARSOL MCX" by HOFFMANN LA ROCHE,

Isopropyl Methoxy cinnamate,

Isoamyl Methoxy cinnamate sold under the trade name "NEO HELIOPAN E 1000" by HAARMANN and REIMER,

Cinoxate, DEA Methoxycinnamate, Diisopropyl Methylcinnamate,

Glyceryl Ethylhexanoate Dimethoxycinnamate

Derivatives of β, β'-diphenylacrylate:

Octocrylene sold in particular under the trade name Uvinul N539 by BASF,

Etocrylene, sold in particular under the trade name Uvinul N35 by BASF,

Derivatives of benzophenone:

Benzophenone-1 sold under the trade name Uvinul 400 by BASF,

Benzophenone-2 sold under the trade name "UVINUL D50" by BASF

Benzophenone-3 or Oxybenzone, sold under the trade name "UVINUL M40" by BASF,

Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF,

Benzophenone-5

Benzophenone-6 sold under the trade name "Helisorb 11" by Norquay

Benzophenone-8 sold under the trade name "Spectra-Sorb UV-24" by American Cyanamid

Benzophenone-9 sold under the trade name "UVINUL DS-49" by BASF,

Benzophenone-12

N-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate.

Derivatives of benzylidene camphor:

3-Benzylidene camphor manufactured under the name "MEXORYL SD" by CHIMEX,

4-Methylbenzylidene camphor sold under the name "EUSOLEX 6300" by MERCK,

Benzylidene Camphor Sulfonic Acid manufactured under the name "MEXORYL SL" by CHIMEX,

Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO" by CHIMEX,

Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name "MEXORYL SX" by CHIMEX,

Polyacrylamidomethyl Benzylidene Camphor manufactured under the name "MEXORYL SW" by CHIMEX,

Derivatives of phenyl benzimidazole:

Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name "Eusolex 232" by Merck,

Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name "NEO HELIOPAN AP" by HAARMANN and REIMER,

Derivatives of the triazine:

Anisotriazine sold under the trade name "Tinosorb S" by CIBA GEIGY,

Ethylhexyl triazone sold in particular under the trade name Uvinul T150 by BASF,

Diethylhexylbutamido triazone sold under the trade name "UVASORB HEB" by SIGMA 3V,

Derivatives of phenyl benzotriazole:

Drometrizole Trisiloxane sold under the name "Silatrizole" by Rhodia Chimie Methylene bis-Benzotriazolyl Tetramethylbutylphenol, sold in solid form under the trade name "MIXXIM BB / 100" by FAIRMOUNT CHEMICAL or in micronized form in aqueous dispersion under the trade name "TINOSORB M" by CIBA SPECIALTY CHEMICALS,

Anthranilic derivatives:

Menthyl anthranilate sold under the trade name "NEO HELIOPAN MA" by HAARMANN and REIMER,

Imidazoline derivatives:

Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate,

Derivatives of benzalmalonate:

Benzalmalonate functional polyorganosiloxanes such as Polysilicone-15 sold under the trade name "PARSOL SLX" by HOFFMANN LA ROCHE

4,4-Diarylbutadiene derivatives:

-1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene

Benzoxazole derivatives:

2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine sold under the name Uvasorb K2A by Sigma 3V;

and their mixtures.

Ethylhexyl Salicylate,

Ethylhexyl Methoxycinnamate

Butyl Methoxydibenzoylmethane

Octocrylene,

Phenylbenzimidazole Sulfonic Acid,

Benzophenone-3,

Benzophenone-4,

Benzophenone-5,

2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle.

4-Methylbenzylidene camphor,

Terephthalylidene Dicamphor Sulfonic Acid,

Disodium Phenyl Dibenzimidazole Tetra-sulfonate,

Anisotriazine,

Ethylhexyl triazone,

Diethylhexyl Butamido Triazone,

Methylène bis-Benzotriazolyl Tetramethylbutylphénol

Drometrizole Trisiloxane

Polysilicone-15

1,1-dicarboxy (2,2'-diméthyl-propyl)-4,4-diphénylbutadiène

2,4-bis-[5-1 (diméthylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imino-1,3,5-triazine

et leurs mélanges.The preferential complementary organic UV filters are chosen from

Ethylhexyl Salicylate,

Ethylhexyl Methoxycinnamate

Butyl Methoxydibenzoylmethane

Octocrylene,

Phenylbenzimidazole Sulfonic Acid,

Benzophenone-3,

Benzophenone-4,

Benzophenone-5,

N-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate.

4-Methylbenzylidene camphor,

Terephthalylidene Dicamphor Sulfonic Acid,

Disodium Phenyl Dibenzimidazole Tetrasulfonate,

Anisotriazine,

Ethylhexyl triazone,

Diethylhexyl Butamido Triazone,

Methylene bis-Benzotriazolyl Tetramethylbutylphenol

Drometrizole Trisiloxane

Polysilicon-15

1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene

2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine

and their mixtures.

The inorganic complementary filters are chosen from pigments or even more nanopigments (average size of primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) coated or uncoated metal oxides such as for example nanopigments of titanium oxide (amorphous or crystallized in rutile form and / or anatase), iron, zinc, zirconium or cerium which are all agents UV photoprotective agents well known per se. Conventional coating agents are also alumina and / or aluminum stearate. Such nanopigments metal oxides, coated or uncoated, are in particular described in patent applications EP518772 and EP518773.

The complementary UV filters according to the invention are generally present in the compositions according to the invention in proportions ranging from 0.01 to 20% by weight relative to the total weight of the composition, and preferably from 0.1 to 10% by weight relative to the total weight of the composition.

The cosmetic compositions according to the invention may furthermore contain agents for tanning and / or artificial tanning of the skin (agents self-tanning agents) such as dihydroxyacetone (DHA).

The compositions in accordance with the present invention may furthermore comprise conventional cosmetic adjuvants, chosen especially from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, humectants, antioxidants, moisturizers, desquamants, agents and the like. anti-free radicals, anti-pollution agents, antibacterials, anti-inflammatory agents, depigmenting agents, pro-pigmentants, opacifiers, stabilizers, emollients, silicones, anti-foam agents, insect repellents, perfumes, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, substance P antagonists, CGRP substance antagonists, fillers, pigments, polymers, propellants, alkalizing or acidifying agents or any other ingredient usually used in the cosmetic and / or dermatological field.
The fatty substances may consist of an oil or a wax or mixtures thereof. By oil is meant a liquid compound at room temperature. By wax is meant a compound that is solid or substantially solid at room temperature and whose melting point is generally greater than 35 ° C.

• les huiles minérales telles que l'huile de paraffine et l'huile de vaseline,
• les huiles d'origine animale telles que le perhydrosqualène,
• les huiles d'origine végétale telles que l'huile d'amande douce, l'huile d'avocat, l'huile de ricin, l'huile d'olive, l'huile de jojoba, l'huile de sésame, l'huile d'arachide, l'huile de pépins de raisin, l'huile de colza, l'huile de coprah, l'huile de noisette, le beurre de karité, l'huile de palme, l'huile de noyau d'abricot, l'huile de calophyllum, l'huile de son de riz, l'huile de germes de maïs, l'huile de germes de blé, l'huile de soja, l'huile de tournesol, l'huile d'onagre, l'huile de carthame, l'huile de passiflore et l'huile de seigle,
• les huiles synthétiques telles que l'huile de purcellin, les esters comme par exemple le myristate de butyle, le myristate d'isopropyle, le myristate de cétyle, le palmitate d'isopropyle, l'adipate d'isopropyle, l'adipate d'éthylhéxyle, le stéarate de butyle, le stéarate d'héxadécyle, le stéarate d'isopropyle, le stéarate d'octyle, le stéarate d'isocétyle, l'oléate de décyle, le laurate d'héxyle, le dicaprylate de propylène glycol et les esters dérivés d'acide lanolique tels que le lanolate d'isopropyle, le lanolate d'isocétyle, les isoparaffines et les poly-a-oléfines.

Among the oils that can be included in the composition of the fatty phase, there may be mentioned in particular:

• mineral oils such as paraffin oil and vaseline oil,
• oils of animal origin such as perhydrosqualene,
• vegetable oils such as sweet almond oil, avocado oil, castor oil, olive oil, jojoba oil, sesame oil, peanut oil, grape seed oil, rapeseed oil, coconut oil, hazelnut oil, shea butter, palm oil, apricot kernel oil , calophyllum oil, rice bran oil, corn germ oil, wheat germ oil, soybean oil, sunflower oil, evening primrose oil, safflower oil, passionflower oil and rye oil,
• synthetic oils such as purcellin oil, esters such as butyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, isopropyl adipate, adipate, ethylhexyl, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, decyl oleate, hexyl laurate, propylene glycol dicaprylate, and the like. esters derived from lanolic acid such as isopropyl lanolate, isocetyl lanolate, isoparaffins and poly-α-olefins.

As other oils that can be used in the compositions according to the invention, mention may also be made of benzoates of C ₁₂ -C ₁₅ fatty alcohols (Finsolv TN of FINETEX), ethers, lipophilic amino acid derivatives, such as N- isopropyl lauroylsarcosinate (Ajinomoto Eldew SL-205), fatty alcohols such as lauryl, cetyl, myristic, stearic, palmitic, oleic alcohol as well as 2-octyldodecanol, acetylglycerides, alcohol octanoates and decanoates and polyalcohols such as glycol and glycerol, ricinoleates of alcohols and polyalcohols such as cetyl, triglycerides of fatty acids such as caprylic / capric triglycerides, saturated fatty acid triglycerides of C ₁₀ -C ₁₈ , fluorinated and perfluorinated oils, lanolin, hydrogenated lanolin, acetylated lanolin and finally silicone oils, volatile or not.

Of course, the fatty phase may also contain one or more conventional lipophilic cosmetic adjuvants, for example waxes, lipophilic gelling agents, surfactants, organic particles or and especially those which are already used in the usual way in manufacturing and obtaining antisolar cosmetic compositions.

Waxy compounds that may be mentioned include paraffin wax, camauba wax and wax bee, hydrogenated castor oil.

Among the organic solvents, mention may be made of lower alcohols and polyols. These can be selected from glycols and glycol ethers such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.

The thickeners may be chosen in particular from crosslinked acrylic polymers such as Carbomer, crosslinked acrylate / C ₁₀ -C ₃₀ alkylacrylate polymers of the Pemulen type or polyacrylate-3 sold under the name VISCOPHOBE DB 1000 by Amerchol; polyacrylamides such as polyacrylamide emulsion, C ₁₃ -C ₁₄ isoparraffine and laureth-7 sold under the name SEPIGEL 305 by SEPPIC, homopolymers or copolymers of AMPS such as HOSTACERIN AMPS sold by CLARIANT, guar gums and celluloses modified or not, such as hydroxypropyl guar gum, methylhydroxyethylcellulose and hydroxypropylmethylcellulose, xanthan gum, nanoscale silica of the Aerosil type.

Of course, those skilled in the art will take care to choose the compound or compounds referred to above and / or their quantities in such a way that the advantageous properties intrinsically attached to the compounds according to the invention are not, or not substantially, impaired by the proposed additions.

The compositions according to the invention can be prepared according to the techniques well known to those skilled in the art, in particular those intended for the preparation emulsions of oil-in-water or water-in-oil type.

This composition may be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / H or W / O / W) such as cream, milk, or in the form of a gel or a cream gel, in the form of a lotion, a oil, powder, solid stick and possibly be packaged in aerosol and be in the form of foam or spray.

Preferably, the compositions according to the invention are in the form an oil-in-water or water-in-oil emulsion.

When it is an emulsion, the aqueous phase thereof can comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins, J. Mol Biol 13, 238 (1965), FR 2 315 991 and FR 2 416 008).

When the cosmetic composition according to the invention is used for the care of the human epidermis, it may be in the form of suspension or dispersion in solvents or fatty substances, in the form of dispersion nonionic vesicle or in the form of an emulsion, preferably of the type oil-in-water, such as cream or milk, in the form of ointment, gel, cream gel, solar oil, solid stick, powder, aerosol foam or spray.

When the cosmetic composition according to the invention is used for the care of hair, it can be in the form of shampoo, lotion, gel, emulsion, non-ionic vesicular dispersion and constitute, for example, a composition to rinse, to apply before or after shampoo, before or after coloring or discoloration, before, during or after permanent or straightening, a styling or treatment lotion or gel, a lotion or a gel for blow drying or setting, a composition of permanent or straightening, of coloring or discoloration of the hair.

When the composition is used as a nail makeup product, lips, eyelashes, eyebrows or skin, such as epidermis, foundation, lipstick stick, eyeshadow, blush, mascara or liner still called "eye liner", it can be in form solid or pasty, anhydrous or aqueous, such as oil-in-water emulsions or water-in-oil, non-ionic vesicular dispersions or suspensions.

As an indication, for the antisolar formulations according to the invention which have an oil-in-water emulsion type support, the aqueous phase (including hydrophilic filters) is usually 50% at 95% by weight, preferably 70 to 90% by weight, relative to the whole of the formulation, the oily phase (including in particular the lipophilic) of 5 to 50% by weight, preferably 10 to 30% by weight, the total formulation, and the (co) emulsifier (s) from 0.5 to 20% by weight, preferably 2 to 10% by weight, based on the set of the formulation.

The compositions according to the invention may be in the form of lotions vaporizable fluids according to the invention and to be applied to the skin or hair in the form of fine particles by means of pressurization. The devices according to the invention are well known those skilled in the art and include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and aerosol pumps using compressed air as a propellant. These are described in the US Patents 4,077,441 and US 4,850,517 (integral to the content of the description).

The compositions packaged in an aerosol according to the invention contain in general, conventional propellants such as, for example, hydrofluorinated compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane, trichlorofluoromethane. They are preferably present in amounts ranging from 15 to 50% by weight per relative to the total weight of the composition.

Another subject of the invention is the use of a compound of formula (I) such that defined above in a cosmetic or dermatological composition such as UV radiation filtering agent.

Another subject of the invention is the use of a compound of formula (I) such that defined above in a cosmetic composition as a control agent the change in skin color due to UV radiation.

Another subject of the invention is the use of a compound of formula (I) such that previously defined as a light stabilizer for polymers synthetic materials such as plastics or glasses, in particular glasses or contact lenses.

Concrete but non-limiting examples illustrating the invention will now to be given.

EXAMPLE 1 Preparation of 2,4,6-tris (4'-amino benzalmalonate di-methyltrimethylsilyl) -s-triazine :

First step: preparation of di-methyltrimethylsilyl malonate

In a reactor surmounted by a Dean Stark, bring to reflux for 3 hours malonic acid (8.3 g, 0.079 mole) and methyltrimethylsilyl alcohol (18.35 g, 0.176 mol) in 50 ml of toluene in the presence of 0.1 ml of acid concentrated sulfuric. The water formed is removed by azeotropy. The sentence organic is washed 3 times with water and is dried over sodium sulfate. After filtration and evaporation of the solvent under vacuum, 22 g of an oil are obtained. colorless. After distillation under vacuum of 0.15 mbar, the fractions are collected. distilling at 74-76 ° C of di-methyltrimethylsilyl malonate (19.6 g, Yield 90%) in the form of a colorless oil and used as it is in the stage next.

Second step: preparation of di-methyltrimethylsilyl 4-nitrobenzalmalonate :

In a balloon equipped with a Dean Stark surmounted by a refrigerant and under nitrogen, the p-nitro benzaldehyde (4.65 g, 0.03 mol) and the dineopentyl malonate (8.5 g, 0.031 mol) in 15 ml of toluene. We add the pre-prepared catalyst, acetic acid (0.2 ml) and piperidine (0.3 ml) suspended in 0.5 ml of toluene. We bring the mixture under stirring at reflux for 5 hours and eliminates via Dean Stark the water formed. Two additions of the same amounts of catalyst were required. The toluene is removed under vacuum, the residue is taken up in ether isopropyl and then washed twice with water. After drying the organic phase and Evaporation of the solvent gives a brown red oil. After purification on a silica column (eluent: Heptane / AcOEt 9: 1), 7.1 g were collected (Yield 57%) of clean fractions of 4-nitrobenzalmalonate di-methyltrimethylsilyl in the form of a pale yellow solid and used as such in the next step.

Third step: preparation of di-methyltrimethylsilyl 4-aminobenzalmalonate

Under stirring and bubbling with nitrogen, the derivative of the previous step is dispersed (3.2 g, 0.0078 mol) in 5.5 ml of acetic acid. 8 ml of water are added. The mixture is heated to 50 ° C. Iron (4.36 g) is added portionwise without exceed a temperature of 55 ° C (introduction time 1 hour). Then we add acetic acid (8 ml) dropwise without exceeding a temperature 55 ° C (1 hour introduction time). An additional 45 minutes is heated to 55 ° C. Cool, add dichloromethane and filter through Celite. The sentence organic is washed with water, with a saturated solution of bicarbonate of sodium, with water and then dried over sodium sulphate. After concentration under reduced pressure an orange oil is obtained which is purified by silica column chromatography (eluent: Heptane / AcOEt 9: 1). We collects 1.8 g (yield 62%) of clean fractions of 4-aminobenzalmalonate di-methyltrimethylsilyl in the form of a yellow solid and used as is in the next step.

Fourth step: preparation of the derivative of Example 1:

Under nitrogen bubbling, the above derivative (1.1 g, 9.66x10 ^-4 mol) dissolved in 5 ml of toluene is introduced at 0-5 ° C. dropwise to a dispersion of cyanuric chloride (0.18 g). g, 3.22x10 ^-4 mol) in 10 ml of toluene. The mixture is then refluxed for 5 hours under nitrogen degassing. After cooling, the organic phase is washed with water and then with an aqueous solution of sodium bicarbonate. Concentrated under reduced pressure. The residue obtained is solubilized in 1,2-dichloroethane. The organic phase is washed with water, with saturated sodium bicarbonate solution, with water and then dried over sodium sulfate. After concentration under reduced pressure, a yellow oil is obtained which is purified by chromatography on a silica column (eluent: Heptane / AcOEt 85:15). 0.75 g (yield 64%) of clean fractions of the derivative of Example 1 are collected in the form of a pale yellow gum: UV (Ethanol) λ _max = 355 nm; ε _max = 118,970; E _1% = 987.

EXAMPLE 2 Preparation of 2,4,6-tris (diethyltrimethylsilyl 4'-amino benzalmalonate) -s-triazine :

Under nitrogen bubbling, diethyl 2,4,6-tris (4'-amino benzalmalonate) -s-triazine (1 g, 1.16 × 10 ^-4 mole) (Example 1 of the EP application) was dissolved. in 5 ml of methyltrimethylsilyl alcohol. Then refluxed for 25 hours with 0.2 g of para toluene sulfonic acid. After addition of 30 ml of dichloromethane, the organic phase is washed with water and then with an aqueous solution of sodium bicarbonate and dried. Concentrated under reduced pressure. The residue obtained is purified by chromatography on a silica column (eluent: Heptane / AcOEt 85:15). 0.35 g (yield 32%) of the derivative of Example 2 is collected in the form of a pale yellow gum: UV (Ethanol) λ _max = 355 nm; ε _max = 125,250; E _1% = 965.

EXAMPLE 3 Preparation of 2,4-bis (4'-amino benzalmalonate di-methyltrimethylsilyl) -6- (para-methoxyphenyl) -s-triazine :

2,4-dichloro-6- (para-methoxy) -s-triazine (0.67 g, 2.61x10 ^-3 mol) is dispersed in 10 ml of toluene. A solution in 10 ml of di-methyltrimethylsilyl 4-aminobenzalmalonate (2 g, 5.2x10 ^-3 mol) is added dropwise under a nitrogen sparge. The mixture is refluxed for 4 hours 30 minutes. After addition of 20 ml of dichloromethane, the organic phase is washed with water, with saturated sodium bicarbonate solution, with water and then dried over sodium sulfate. The organic phase is concentrated under vacuum. The residue is separated on a silica column (eluent: Heptane / EtOAc 8: 2). Clean fractions are recovered as a pale yellow oil which is precipitated from Ethanol / Heptane to give the derivative of Example 3 (1.42 g, Yield 58%) as a yellow powder. pale amorphous: UV (Ethanol) λ _max = 351 nm; ε _max = 74,540; E _1% = 791, λ _max = 340 nm; ε _max = 74,450; E _1% = 790, λ _max = 296 nm; ε _max = 28,280; E _1% = 340.

EXAMPLE 4 Preparation of 2,4-bis (4'-amino benzalmalonate di-methyltrimethylsilyl) -6- (2'-aminobenzimidazole) -s-triazine :

First step: preparation of 2,4-dichloro-6- (2'-aminobenzimidazole) -s-triazine :

Cyanuric chloride (18 g, 0.097 mol) is solubilized at 0 ° C. in 150 ml. of acetone. 50 ml of water are added. A suspension of 2-aminobenzimidazole (13 g, 0.097 mol) in 100 ml of acetone is added dropwise under Nitrogen bubbled at 0 ° C. A solution of sodium carbonate (7 g) is added in 150 ml of water. The heterogeneous mixture is left stirring at 0-5 ° C. during 2 hours. The reaction mixture is filtered. The solid is washed dichloromethane, with water and with a little acetone. After drying, we recover 25 g (91% yield) of 2,4-dichloro-6- (2'-aminobenzimidazole) -s-triazine in the form of a beige powder and used as such in the next step.

Second step: preparation of the derivative of Example 4

The preceding derivative (0.267 g, 9.5x10 ^-4 mol) is dispersed with 4-aminobenzalmalonate di-methyltrimethylsilyl methyltrimethylsilyl (0.72 g, 1.9x10 ^-3 mol) in 10 ml of toluene. The mixture is refluxed for 4 hours 30 minutes. The organic phase is concentrated under vacuum. After addition of 20 ml of dichloromethane, the organic phase is washed with water, with saturated sodium bicarbonate solution, with water and then dried over sodium sulfate. After crystallization from a dichloromethane / MeOH mixture, the derivative of Example 4 (0.66 g, yield 72%) is obtained in the form of an amorphous light brown powder: UV (Ethanol) λ _max = 342 nm; ε _max = 61,910; E _1% = 640, λ _max = 325 nm; ε _max = 76,420; E _1% = 790.

EXAMPLE OF FORMULATION IN O / W EMULSION

CHEMICAL DENOMINATION COMMERCIAL REFERENCE - Supplier Composition (g%) GLYCERYLE MONO-STEARATE MIXTURE / POLYETHYLENE GLYCOL STEARATE (100 OE) SIMULSOL 165 - Seppic 1 STEARINE STEARINE ACID TP 1200 PASTILLES - Stearinerie Dubois 1.5 POLY DIMETHYLSILOXANE 200 FLUID 350 CS - Dow Corning 0.5 CETYLIC ALCOHOL LANETTE 16 NF - Cognis 0.5 CETYLSTEARYL GLUCOSIDE / CETYLSTEARYL ALCOHOL MIXTURE MONTANOV 68 - Seppic 2 TORY 1 TRIETHANOLAMINE TRIETHANOLAMINE - BASF 0.45 CAPRIC ACID TRIGLYCERIDE / CAPRILIC MYRITOL 317 - Cognis 10 COMPOUND OF EXAMPLE 1 5 GLYCERINE PRICERINE 9091 - Uniquema 5 XANTHANE GUM KELTROL T - CP kelco 0.1 ACRYLIC ACIDIC ACRYLIC COPOLYMER (C10 / C30) RETICLE PEMULEN TR-1 - Noveon 0.12 TRIETHANOLAMINE TRIETHANOLAMINE - BASF qs pH DEMINERALIZED WATER qsp 100g

PHOTOSTABILITIES COMPARE BETWEEN A COMPOUND OF ART PRIOR ART AND THE COMPOUND ACCORDING TO THE INVENTION OF EXAMPLE 1 Products tested:

2,4,6-tris (diisobutyl 4'-amino benzalmalonate) -s-triazine = interior art (Example 1 of EP507691).

2,4,6-tris (di-methyltrimethylsilyl 4'-amino benzalmalonate) -s-triazine = Example 1 according to the invention.

The two products were dissolved in 5% by weight in Miglyol 812 oil. About 10 mg of oily solution are spread over 10 cm ² on the surface of a hollow disc of etched glass; the quantity is determined by weighing.

The films of the oily solutions are irradiated for one hour using an ORIEL solar emulator (UVA = 14.2 mW / cm ² , UVB = 0.41 mW / cm ² ), then extracted with 10 ml of ethanol. 10% isopropanol and 5 min sonication. The product quantifications are made by HPLC extracts.

HPLC conditions: column: UP5WOD-25QS, 250 * 4.6 mm, 5 μm, Interchrom; eluent: methanol (Comparative Example 1) and 96% methanol + 4% water (Example 1) Flow rate: 1 ml / min; volume injected: 10 μl; detection: Barrette de diodes; tr (min): 5.2 (Comparative Example 1) and 13.8 (Example 1).

Loss rates are determined by comparing product quantities present in the irradiated samples and in the non-irradiated prepared controls simultaneously and treated in the same way (averages over 3 samples; S = area / mg solution):% loss = 100 * (S0 - Sirr) / S0

PHOTOSTABILITY RESULTS

compounds Trial % of disappearance Compound (prior art) 1 11 Compound (prior art) 2 10 Compound (prior art) 3 9 Example 1 4 0 Example 1 5 0 Example 1 6 0

Compound of the Prior Art: The loss in Miglyol is between 9 and 11% after one hour of exposure to the simulator of a film of 1 mg / cm ² of 5% solution.

Example 1: No loss in Miglyol is observed after one hour of exposure to the simulator of a 1 mg / cm ^{2 film} of 5% solution.

Claims (20)

Compound corresponding to the following general formula (I):

in which : the radicals R ₁ , R ₂ and R _{3, which may be} identical or different, represent a linear or branched, saturated or unsaturated C ₁ -C ₁₀ alkyl radical which may comprise one or more halogen atoms; a phenyl radical, p is 0 or 1, A is hydrogen; a linear or branched, saturated or unsaturated C ₁ -C ₈ alkyl radical; a phenyl radical; the group Si (CH ₃ ) ₃ , provided that when A is Si (CH ₃ ) ₃ , then p = 0 and R ₁ , R ₂ and R ₃ are methyl, W is a linear or branched, saturated or unsaturated C ₁ -C ₈ alkylene radical, optionally substituted with a hydroxyl radical, Z is - (C = O) OR ₄ , - (C = O) R ₅ , - (C = O) NR ₆ R ₇ , -SO ₂ R ₈ , -CN or - (C = O) YCHA (W) _p SiR ₁ R ₂ R ₃ , the radical R ₄ denotes hydrogen; a linear or branched, saturated or unsaturated C ₁ -C ₂₀ alkyl radical, the radical R ₅ denotes a linear or branched, optionally cyclic, C ₁ -C ₂₀ alkyl radical; a C ₆ -C ₁₂ aryl, the radicals R ₆ , R ₇ , which may be identical or different, represent hydrogen; a linear or branched C ₁ -C ₂₀ alkyl, Y denotes -O- or -NR ₇ -, the radical R ₈ denotes a linear or branched C ₁ -C ₂₀ alkyl radical; a C ₆ -C ₁₂ aryl. B ₁ denotes a chromophoric group chosen from those of the para amino benzalmalonate, amino benzimidazole, benzimidazole, amino benzoate, amino salicylate, anthranilate, amino benzylidene camphor, amino benzotriazole, amino benzoxazole, para aminophenyl benzoxazole type; B ₁ may denote a linear or branched C ₁ -C ₂₀ aminoalkyl group; a C ₆ -C ₂₀ aryl group substituted or unsubstituted with alkyl, hydroxy and alkoxy radicals. Compound according to claim 1, wherein B ₁ denotes a group of formula (II) below:

in which Z, A, p, W, R ₁ , R ₂ and R ₃ have the same meanings given in claim 1. Compound according to claim 1 or 2, having at least one, and even more preferably all, of the following characteristics: Z = - (C = O) OR ₅ , -CN or (C = O) YCHA (W) _p SiR ₂ R ₃ R ₄ , R ₅ is methyl or ethyl, A is H, R ₂ to R ₄ denote C ₁ -C ₄ alkyl and more preferably methyl, n is 0, p is 0 or 1, W is a C ₁ -C ₂ alkylene radical. Compound according to claim 3, selected from the following compounds:

Cosmetic or dermatological composition, intended for the photoprotection of keratin materials, characterized in that it contains in a cosmetically acceptable support at least one compound of formula (I) as defined in any one of claims 1 to 4. Composition according to Claim 5, characterized in that the compound of formula (I) is present in the composition at a content ranging from 0.01% to 20% by weight, relative to the total weight of the composition, preferably ranging from 0.1% to 10% by weight, relative to the total weight of the composition. Composition according to Claim 5 or 6, characterized in that the said cosmetically acceptable support is in the form of an oil-in-water or water-in-oil emulsion. Composition according to any one of Claims 5 to 7, characterized in that it further comprises one or more additional organic or inorganic filters active in the UV-A and / or UV-B range. Composition according to Claim 8, characterized in that the said complementary organic screening agents are chosen from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives other than those defined in the preceding claims; benzophenone derivatives; derivatives of β, β-diphenylacrylate; benzotriazole derivatives; benzalmalonate derivatives other than those defined in the preceding claims; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives; benzoxazole derivatives, p-aminobenzoic acid derivatives (PABA); methylene bis (hydroxyphenyl benzotriazole) derivatives; benzoxazole derivatives; filter polymers and silicone filters; dimers derived from α-alkylstyrene; 4,4-diarylbutadienes and mixtures thereof. Composition according to Claim 9, characterized in that the said complementary organic screening agents are chosen from Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate Butyl Methoxydibenzoylmethane Octocrylene, Phenylbenzimidazole Sulfonic Acid, Benzophenone-3, Benzophenone-4, Benzophenone-5, N-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate. 4-Methylbenzylidene camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine Anisotriazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, Methylene bis-Benzotriazolyl Tetramethylbutylphenol Drometrizole Trisiloxane Polysilicon-15 1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine and their mixtures. Composition according to Claim 10, characterized in that the inorganic complementary filters are pigments or nanopigments of metal oxides, coated or uncoated. Composition according to Claim 11, characterized in that the said pigments or nanopigments are chosen from titanium, zinc, iron, zirconium and cerium oxides and mixtures thereof, coated or otherwise. Composition according to any one of Claims 1 to 12, characterized in that it also comprises at least one agent for tanning and / or artificial browning of the skin. Composition according to any one of Claims 1 to 13, characterized in that it additionally comprises at least one adjuvant chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, humectants, antioxidants, moisturizers, desquamants, anti-radical agents, antipollution agents, antibacterials, anti-inflammatory agents, depigmenting agents, pro-pigmentants, opacifiers, stabilizers, emollients, silicones, anti-agents foam, insect repellents, perfumes, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, substance P antagonists, CGRP antagonists, fillers, pigments, polymers , propellants, alkalizing agents or acidifying agents Composition according to any one of Claims 1 to 14, characterized in that it is a composition that protects the human epidermis or an antisolar composition and that it is in the form of a dispersion nonionic vesicle, an emulsion, in particular an oil-in-water emulsion, a cream, a milk, a gel, a cream gel, a suspension, a dispersion, an oil, a powder, a solid stick, a foam or a spray. Composition according to any one of Claims 1 to 14, characterized in that it is a makeup composition for eyelashes, eyebrows, nails or skin and that it is in solid form or paste, anhydrous or aqueous, an emulsion, a suspension or a dispersion. Composition according to any one of Claims 1 to 14, characterized in that it is a composition intended for the protection of the hair against ultraviolet rays and that it is in the form of a shampoo, a lotion, a gel, an emulsion, a nonionic vesicular dispersion. Use of a compound of formula (I) as defined in any one Claims 1 to 4 in a cosmetic or dermatological composition as a filtering agent for UV radiation. Use of a compound of formula (I) as defined in any one Claims 1 to 4 in a cosmetic composition as agent for control of the variation of skin color due to UV radiation. Use of a compound of formula (I) as defined in any one Claims 1 to 4 as a light-stabilizing agent for polymers synthetic or glass.